Cavallo worked with George Massenburg at The Complex Recording Studios early in his career. He joined Warner Bros. Records as A&R representative in 1987 and worked with Black Sabbath as one of his first assignments.[4][9] He also signed both the Goo Goo Dolls and Green Day during his first tenure at Warner Bros. Records.[4][10] Cavallo became senior vice-president of A&R of Hollywood Records in 1998.[11] He moved to Warner Music Group in 2002 and became chief creative officer of the company in 2009.[11] Cavallo became chairman of Warner Bros. Records in 2010.[11]

Two Cavallo-produced Goo Goo Dolls tracks, "Iris" and "Slide," were included in Billboard's top 100 pop songs 1992–2012.[36] "Iris" was the top pop song from 1992–2012 and "Slide" was ninth-best according to Billboard's list.[36]

Cavallo has won three Grammy awards: 1998 Producer of the Year; 2004 Best Rock Album for producing Green Day’s American Idiot; and 2005 Record of the Year for producing Green Day’s "Boulevard of Broken Dreams".[5]